基于分子工程能量转移构建的比率型双光子荧光探针在生物成像中的应用（英文）
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摘要
设计和合成可被应用于生物系统中各种分析物的比例检测与成像的基于能量转移二元体系的比率型双光子荧光探针是一项至关重要的任务。因此,对近10 a基于荧光共振能量转移(FRET)或跨键能量转移(TBET)构建的比率型双光子荧光探针在生物成像中的应用进行综述。未来的研究方向是基于FRET/TBET构建新型双光子比率型荧光探针,并将其应用于生物分析和疾病诊断领域。
Design and synthesis of energy transfer dyads-based ratiometric TP fluorescent probe for the ratiometric detection and imaging of various analytes in biological systems is a vital task. A general introduction to molecular engineering of the fluorescence resonance energy transfer(FRET), and through-bond energy transfer(TBET)-based ratiometric TP fluorescent probe for bioimaging applications during the past decade were reviewed. It was suggested that more attention would be committed to development of new FRET/TBET-based ratiometric TP dyads and applications of two-photon fluorescence microscope(TPFM) in areas of bioanalysis and disease diagnosis.
Design and synthesis of energy transfer dyads-based ratiometric TP fluorescent probe for the ratiometric detection and imaging of various analytes in biological systems is a vital task. A general introduction to molecular engineering of the fluorescence resonance energy transfer(FRET), and through-bond energy transfer(TBET)-based ratiometric TP fluorescent probe for bioimaging applications during the past decade were reviewed. It was suggested that more attention would be committed to development of new FRET/TBET-based ratiometric TP dyads and applications of two-photon fluorescence microscope(TPFM) in areas of bioanalysis and disease diagnosis.
引文
[1]KIM J S,QUANG D T.Calixarene-Derived Fluorescent Probes[J].Chemical Reviews,2007,107(9):3780-3799.
[2]NOLAN E M,LIPPARD S J.Tools and Tactics for the Optical Detection of Mercuric Ion[J].Chemical Reviews,2008,108(9):3443-3480.
[3]CHEN X,ZHOU Y,PENG X,et al.Fluorescent and Colorimetric Probes for Detection of Thiols[J].Chemical Society Reviews,2010,39(6):2120-2135.
[4]ZHOU Y,XU Z,YOON J.Fluorescent and Colorimteric Chemosensors for Detection of Nucleotides,FAD and NADH:Highlighted Research During 2004-2010[J].Chemical Society Reviews,2011,40(5):2222-2235.
[5]KIM H N,GUO Z,ZHU W,et al.Recent Progress on Polymer-Based Fluorescent and Colorimetric Chemosensors[J].Chemical Society Reviews,2011,40(1):79-93.
[6]KIM H M,CHO B R.Small-Molecule Two-Photon Probes for Bioimaging Applications[J].Chemical Reviews,2015,115(11):5014-5055.
[7]HELMCHEN F,DENK W.Deep Tissue Two-Photon Microscopy[J].Nature Methods,2005,2(12):932-940.
[8]SO P T C,DONG C Y,MASTERS B R,et al.TwoPhoton Excitation Fluorescence Microscopy[J].Annual Review of Biomedical Engineering,2000(2):399-429.
[9]KIM H M,CHO B R.Two-Photon Fluorescent Probes for Metal Ions[J].Chemistry-An Asian Journal,2011,6(1):58-69.
[10]KIM H M,CHO B R.Two-Photon Probes for Intracellular Free Metal Ions,Acidic Vesicles,and Lipid Rafts in Live Tissues[J].Accounts of Chemical Research,2009,42(7):863-872.
[11]XU Z,BAEK K H,KIM H N,et al.Zn2+-Triggered Amide Tautomerization Produces a Highly Zn2+-Selective,Cell-Permeable,and Ratiometric Fluorescent Sensor[J].Journal of the American Chemical Society,2009,132(2):601-610.
[12]HAN Z X,ZHANG X B,LI Z,et al.Efficient Fluorescence Resonance Energy Transfer-Based Ratiometric Fluorescent Cellular Imaging Probe For Zn2+Using a Rhodamine Spirolactam as a Trigger[J].Analytical Chemistry,2010,82(8):3108-3113.
[13]ZHAO Y,ZHANG X B,HAN Z X,et al.Highly Sensitive and Selective Colorimetric and Off-On Fluorescent Chemosensor for Cu2+in Aqueous Solution and Living Cells[J].Analytical Chemistry,2009,81(16):7022-7030.
[14]LI C Y,ZHANG X B,QIAO L,et al.NaphthalimidePorphyrin Hybrid Based Ratiometric Bioimaging Probe for Hg2+:Well-Resolved Emission Spectra and Unique Specificity[J].Analytical Chemistry,2009,81(24):9993-10001.
[15]LIU J Y,YEUNG H S,XU W,et al.Highly Efficient Energy Transfer in Subphthalocyanine-BODIPYConjugates[J].Organic Letters,2008,10(23):5421-5424.
[16]KUMAR M,KUMAR N,BHALLA V,et al.Naphthalimide Appended Rhodamine Derivative:Through Bond Energy Transfer for Sensing of Hg2+Ions[J].Organic Letters,2011,13(6):1422-1425.
[17]JIAO G S,THORESEN L H,BURGESS K.Fluorescent,Through-Bond Energy Transfer Cassettes for Labeling Multiple Biological Molecules in One Experiment[J].Journal of the American Chemical Society,2003,125(48):14668-14669.
[18]PELEG A,CHUNG Y.Cross-Talk Dynamics of Optical Solitons in Multichannel Waveguide Systems with a Ginzburg-Landau Gain-Loss Profile[J].Physical Review A,2012,85(6).doi:10.1103/PhysRevA.85.063828.
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[20]PANG J J,GAO F,WU S M.Cross-Talk Between ONand OFF Channels in the Salamander Retina:Indirect Bipolar Cell Inputs to ON-OFF Ganglion Cells[J].Vision Research,2007,47(3):384-392.
[21]QIAN L H,LI L,YAO S Q.Two-Photon Small Molecule Enzymatic Probes[J].Accounts of Chemical Research,2016,49(4):626-634.
[22]SUMALEKSHMY S,FAHRNI C J.Metal-Ion-Responsive Fluorescent Probes for Two-Photon Excitation Microscopy[J].Chemistry of Materials,2010,23(3):483-500.
[23]LIU H W,LIU Y,WANG P,et al.Molecular Engineering of Two-Photon Fluorescent Probes for Bioimaging Appl i ca t ions[J].Methods and Appl i c at ions in Fluorescence,2017,5(1).doi:10.1088/2050-6120/aa61b0.
[24]KIM H M,CHO B R.Mitochondrial-Targeted TwoPhoton Fluorescent Probes for Zinc Ions,and Thiols in Living Tissues[J].Oxidative Medicine and Cellular Longevity,2013.doi:10.1155/2013/323619.
[25]ALBOTA M,BELJONNE D,BRéDAS J L,et al.Design of Organic Molecules with Large Two-Photon Absorption Cross Sections[J].Science,1998,281(5383):1653-1656.
[26]XU C,WEBB W W.Measurement of Two-Photon Excitation Cross Sections of Molecular Fluorophores with Data from 690 to 1 050 nm[J].Journal of the Optical Society of America B:Optical Physics,1996,13(3):481-491.
[27]ALBOTA M A,XU C,WEBB W W.Two-Photon Fluorescence Excitation Cross Sections of Biomolecular Probes from 690 to 960 nm[J].Applied Optics,1998,37(31):7352-7356.
[28]DE SILVA A P,GUNARATNE H Q,GUNNLAUGSSONT,et al.Signaling Recognition Events with Fluorescent Sensors and Switches[J].Chemical Reviews,1997,97(5):1515-1566.
[29]KIM J S,QUANG D T.Calixarene-Derived Fluorescent Probes[J].Chemical Reviews,2007,107(9):3780-3799.
[30]FAN J,HU M,ZHAN P,et al.Energy Transfer Cassettes Based on Organic Fluorophores:Construction and Applications in Ratiometric Sensing[J].Chemical Society Reviews,2013,42(1):29-43.
[31]FENG Y,CHENG J H,ZHOU L,et al.Ratiometric Optical Oxygen Sensing:A Review in Respect of Material Design[J].Analyst,2012,137(21):4885-4901.
[32]STRYER L,HAUGLAND R P.Energy Transfer:ASpectroscopic Ruler[C]//Proceedings of the National Academy of Sciences of the United States of America.[S.l.]:National Academy of Sciences,1967,58(2):719-726.
[33]OEVERING H,PADDON-ROW M N,HEPPENERM,et al.Long-Range Photoinduced Through-Bond Electron Transfer and Radiative Recombination Via Rigid Nonconjugated Bridges:Distance and Solvent Dependence[J].Journal of the American Chemical Society,1987,109(11):3258-3269.
[34]ZHOU Z G,LI Y,WU Y Q.Ratiometric Fluorescence Probe for Two-Photon Bioimaging of Cr3+in Living Cells[J].Tetrahedron Letters,2014,55(30):4075-4077.
[35]YUAN L,JIN F,ZENG Z,et al.Engineering a FRET Strategy to Achieve a Ratiometric Two-Photon Fluorescence Response with a Large Emission Shift and Its Application to Fluorescence Imaging[J].Chemical Science,2015,6(4):2360-2365.
[36]ZHU X Y,ZHU L M,LIU H W,et al.A TwoPhoton Fluorescent Turn-On Probe for Imaging of SO2Derivatives in Living Cells and Tissues[J].Analytica Chimica Acta,2016,937:136-142.
[37]YANG X,ZHOU Y,ZHANG X,et al.A TP-FRETBased Two-Photon Fluorescent Probe for Ratiometric Visualization of Endogenous Sulfur Dioxide Derivatives in Mitochondria of Living Cells and Tissues[J].Chemical Communications,2016,52(67):10289-10292.
[38]ZHOU L,LU D Q,WANG Q,et al.An Efficient Two-Photon Ratiometric Fluorescent Probe Platform for Dual-Channel Imaging of Lysosomes in Living Cells and Tissues[J].Sensors and Actuators B:Chemical,2017,238:274-280.
[39]ZHU X,XIONG M,LIU H,et al.A FRET-Based Ratiometric Two-Photon Fluorescent Probe for DualChannel Imaging of Nitroxyl in Living Cells and Tissues[J].Chemical Communications,2016,52(4):733-736.
[40]ZHOU Y,ZHANG X,YANG S,et al.Ratiometric Visualization of NO/H2S Cross-Talk in Living Cells and Tissues Using a Nitroxyl-Responsive Two-Photon Fluorescence Probe[J].Analytical Chemistry,2017,89(8):4587-4594.
[41]ZHANG J,ZHU X Y,HU X X,et al.Ratiometric Two-Photon Fluorescent Probe for in Vivo Hydrogen P o l y s u l f i d e s De t e c t i o n a n d Ima g i n g Du r i n g Lipopolysaccharide-Induced Acute Organs Injury[J].Analytical Chemistry,2016,88(23):11892-11899.
[42]ZHANG H,WANG C,WANG G,et al.ThrombinMediated Ratiometric Two-Photon Fluorescent Probe for Selective Imaging of Endogenous Ultratrace Glutathione in Platelet[J].Biosensors and Bioelectronics,2016,78:344-350.
[43]DONG B,SONG X Z,KONG X Q,et al.Simultaneous Near-Infrared and Two-Photon in Vivo Imaging of H2O2 Using a Ratiometric Fluorescent Probe Based on the Unique Oxidative Rearrangement of Oxonium[J].Advanced Materials,2016,28(39):8755-8759.
[44]CHENG D,PAN Y,WANG L,et al.Selective Visualization of the Endogenous Peroxynitrite in an Inflamed Mouse Model by a Mitochondria-Targetable Two-Photon Ratiometric Fluorescent Probe[J].Journal of the American Chemical Society,2017,139(1):285-292.
[45]ZHOU L,ZHANG X,WANG Q,et al.Molecular Engineering of a TBET-Based Two-Photon Fluorescent Probe for Ratiometric Imaging of Living Cells and Tissues[J].Journal of the American Chemical Society,2014,136(28):9838-9841.
[46]ZHOU L,WANG Q,ZHANG X B,et al.ThroughBond Energy Transfer-Based Ratiometric Two-Photon Probe for Fluorescent Imaging of Pd2+Ions in Living Cells and Tissues[J].Analytical Chemistry,2015,87(8):4503-4507.
[47]ZHOU L Y,LIU Y C,HU S Q,et al.A New Ratiometric Two-Photon Fluorescent Probe for Imaging of Lysosomes in Living Cells and Tissues[J].Tetrahedron,2016,72(31):4637-4642.
[48]WANG J,LI B,ZHAO W,et al.Two-Photon Near Infrared Fluorescent Turn-On Probe Toward Cysteine and Its Imaging Applications[J].ACS Sensors,2016,1(7):882-887.
[49]SUN W,FAN J L,HU C,et al.A Two-Photon Fluorescent Probe with Near-Infrared Emission for Hydrogen Sulfide Imaging in Biosystems[J].Chemical Communications,2013,49(37):3890-3892.
[50]ZHOU L Y,LU D Q,WANG Q Q,et al.Molecular Engineering of a Mitochondrial-Targeting Two-Photon in and Near-Infrared Out Fluorescent Probe for Gaseous Signal Molecules H2S in Deep Tissue Bioimaging[J].Biosensors and Bioelectronics,2017,91:699-705.
[51]ZHOU L Y,WANG Q Q,TAN Y,et al.Rational Development of Near-Infrared Fluorophores with Large Stokes Shifts,Bright One-Photon and Two-Photon Emissions for Bioimaging and Biosensing Applications[J].Chemistry-A European Journal,2017,23(36):8736-8740.
[2]NOLAN E M,LIPPARD S J.Tools and Tactics for the Optical Detection of Mercuric Ion[J].Chemical Reviews,2008,108(9):3443-3480.
[3]CHEN X,ZHOU Y,PENG X,et al.Fluorescent and Colorimetric Probes for Detection of Thiols[J].Chemical Society Reviews,2010,39(6):2120-2135.
[4]ZHOU Y,XU Z,YOON J.Fluorescent and Colorimteric Chemosensors for Detection of Nucleotides,FAD and NADH:Highlighted Research During 2004-2010[J].Chemical Society Reviews,2011,40(5):2222-2235.
[5]KIM H N,GUO Z,ZHU W,et al.Recent Progress on Polymer-Based Fluorescent and Colorimetric Chemosensors[J].Chemical Society Reviews,2011,40(1):79-93.
[6]KIM H M,CHO B R.Small-Molecule Two-Photon Probes for Bioimaging Applications[J].Chemical Reviews,2015,115(11):5014-5055.
[7]HELMCHEN F,DENK W.Deep Tissue Two-Photon Microscopy[J].Nature Methods,2005,2(12):932-940.
[8]SO P T C,DONG C Y,MASTERS B R,et al.TwoPhoton Excitation Fluorescence Microscopy[J].Annual Review of Biomedical Engineering,2000(2):399-429.
[9]KIM H M,CHO B R.Two-Photon Fluorescent Probes for Metal Ions[J].Chemistry-An Asian Journal,2011,6(1):58-69.
[10]KIM H M,CHO B R.Two-Photon Probes for Intracellular Free Metal Ions,Acidic Vesicles,and Lipid Rafts in Live Tissues[J].Accounts of Chemical Research,2009,42(7):863-872.
[11]XU Z,BAEK K H,KIM H N,et al.Zn2+-Triggered Amide Tautomerization Produces a Highly Zn2+-Selective,Cell-Permeable,and Ratiometric Fluorescent Sensor[J].Journal of the American Chemical Society,2009,132(2):601-610.
[12]HAN Z X,ZHANG X B,LI Z,et al.Efficient Fluorescence Resonance Energy Transfer-Based Ratiometric Fluorescent Cellular Imaging Probe For Zn2+Using a Rhodamine Spirolactam as a Trigger[J].Analytical Chemistry,2010,82(8):3108-3113.
[13]ZHAO Y,ZHANG X B,HAN Z X,et al.Highly Sensitive and Selective Colorimetric and Off-On Fluorescent Chemosensor for Cu2+in Aqueous Solution and Living Cells[J].Analytical Chemistry,2009,81(16):7022-7030.
[14]LI C Y,ZHANG X B,QIAO L,et al.NaphthalimidePorphyrin Hybrid Based Ratiometric Bioimaging Probe for Hg2+:Well-Resolved Emission Spectra and Unique Specificity[J].Analytical Chemistry,2009,81(24):9993-10001.
[15]LIU J Y,YEUNG H S,XU W,et al.Highly Efficient Energy Transfer in Subphthalocyanine-BODIPYConjugates[J].Organic Letters,2008,10(23):5421-5424.
[16]KUMAR M,KUMAR N,BHALLA V,et al.Naphthalimide Appended Rhodamine Derivative:Through Bond Energy Transfer for Sensing of Hg2+Ions[J].Organic Letters,2011,13(6):1422-1425.
[17]JIAO G S,THORESEN L H,BURGESS K.Fluorescent,Through-Bond Energy Transfer Cassettes for Labeling Multiple Biological Molecules in One Experiment[J].Journal of the American Chemical Society,2003,125(48):14668-14669.
[18]PELEG A,CHUNG Y.Cross-Talk Dynamics of Optical Solitons in Multichannel Waveguide Systems with a Ginzburg-Landau Gain-Loss Profile[J].Physical Review A,2012,85(6).doi:10.1103/PhysRevA.85.063828.
[19]JIN M,BERROUT J,CHEN L,et al.HypotonicityInduced TRPV4 Function in Renal Collecting Duct Cells:Modulation by Progressive Cross-Talk with Ca2+-Activated K+Channels[J].Cell Calcium,2012,51(2):131-139.
[20]PANG J J,GAO F,WU S M.Cross-Talk Between ONand OFF Channels in the Salamander Retina:Indirect Bipolar Cell Inputs to ON-OFF Ganglion Cells[J].Vision Research,2007,47(3):384-392.
[21]QIAN L H,LI L,YAO S Q.Two-Photon Small Molecule Enzymatic Probes[J].Accounts of Chemical Research,2016,49(4):626-634.
[22]SUMALEKSHMY S,FAHRNI C J.Metal-Ion-Responsive Fluorescent Probes for Two-Photon Excitation Microscopy[J].Chemistry of Materials,2010,23(3):483-500.
[23]LIU H W,LIU Y,WANG P,et al.Molecular Engineering of Two-Photon Fluorescent Probes for Bioimaging Appl i ca t ions[J].Methods and Appl i c at ions in Fluorescence,2017,5(1).doi:10.1088/2050-6120/aa61b0.
[24]KIM H M,CHO B R.Mitochondrial-Targeted TwoPhoton Fluorescent Probes for Zinc Ions,and Thiols in Living Tissues[J].Oxidative Medicine and Cellular Longevity,2013.doi:10.1155/2013/323619.
[25]ALBOTA M,BELJONNE D,BRéDAS J L,et al.Design of Organic Molecules with Large Two-Photon Absorption Cross Sections[J].Science,1998,281(5383):1653-1656.
[26]XU C,WEBB W W.Measurement of Two-Photon Excitation Cross Sections of Molecular Fluorophores with Data from 690 to 1 050 nm[J].Journal of the Optical Society of America B:Optical Physics,1996,13(3):481-491.
[27]ALBOTA M A,XU C,WEBB W W.Two-Photon Fluorescence Excitation Cross Sections of Biomolecular Probes from 690 to 960 nm[J].Applied Optics,1998,37(31):7352-7356.
[28]DE SILVA A P,GUNARATNE H Q,GUNNLAUGSSONT,et al.Signaling Recognition Events with Fluorescent Sensors and Switches[J].Chemical Reviews,1997,97(5):1515-1566.
[29]KIM J S,QUANG D T.Calixarene-Derived Fluorescent Probes[J].Chemical Reviews,2007,107(9):3780-3799.
[30]FAN J,HU M,ZHAN P,et al.Energy Transfer Cassettes Based on Organic Fluorophores:Construction and Applications in Ratiometric Sensing[J].Chemical Society Reviews,2013,42(1):29-43.
[31]FENG Y,CHENG J H,ZHOU L,et al.Ratiometric Optical Oxygen Sensing:A Review in Respect of Material Design[J].Analyst,2012,137(21):4885-4901.
[32]STRYER L,HAUGLAND R P.Energy Transfer:ASpectroscopic Ruler[C]//Proceedings of the National Academy of Sciences of the United States of America.[S.l.]:National Academy of Sciences,1967,58(2):719-726.
[33]OEVERING H,PADDON-ROW M N,HEPPENERM,et al.Long-Range Photoinduced Through-Bond Electron Transfer and Radiative Recombination Via Rigid Nonconjugated Bridges:Distance and Solvent Dependence[J].Journal of the American Chemical Society,1987,109(11):3258-3269.
[34]ZHOU Z G,LI Y,WU Y Q.Ratiometric Fluorescence Probe for Two-Photon Bioimaging of Cr3+in Living Cells[J].Tetrahedron Letters,2014,55(30):4075-4077.
[35]YUAN L,JIN F,ZENG Z,et al.Engineering a FRET Strategy to Achieve a Ratiometric Two-Photon Fluorescence Response with a Large Emission Shift and Its Application to Fluorescence Imaging[J].Chemical Science,2015,6(4):2360-2365.
[36]ZHU X Y,ZHU L M,LIU H W,et al.A TwoPhoton Fluorescent Turn-On Probe for Imaging of SO2Derivatives in Living Cells and Tissues[J].Analytica Chimica Acta,2016,937:136-142.
[37]YANG X,ZHOU Y,ZHANG X,et al.A TP-FRETBased Two-Photon Fluorescent Probe for Ratiometric Visualization of Endogenous Sulfur Dioxide Derivatives in Mitochondria of Living Cells and Tissues[J].Chemical Communications,2016,52(67):10289-10292.
[38]ZHOU L,LU D Q,WANG Q,et al.An Efficient Two-Photon Ratiometric Fluorescent Probe Platform for Dual-Channel Imaging of Lysosomes in Living Cells and Tissues[J].Sensors and Actuators B:Chemical,2017,238:274-280.
[39]ZHU X,XIONG M,LIU H,et al.A FRET-Based Ratiometric Two-Photon Fluorescent Probe for DualChannel Imaging of Nitroxyl in Living Cells and Tissues[J].Chemical Communications,2016,52(4):733-736.
[40]ZHOU Y,ZHANG X,YANG S,et al.Ratiometric Visualization of NO/H2S Cross-Talk in Living Cells and Tissues Using a Nitroxyl-Responsive Two-Photon Fluorescence Probe[J].Analytical Chemistry,2017,89(8):4587-4594.
[41]ZHANG J,ZHU X Y,HU X X,et al.Ratiometric Two-Photon Fluorescent Probe for in Vivo Hydrogen P o l y s u l f i d e s De t e c t i o n a n d Ima g i n g Du r i n g Lipopolysaccharide-Induced Acute Organs Injury[J].Analytical Chemistry,2016,88(23):11892-11899.
[42]ZHANG H,WANG C,WANG G,et al.ThrombinMediated Ratiometric Two-Photon Fluorescent Probe for Selective Imaging of Endogenous Ultratrace Glutathione in Platelet[J].Biosensors and Bioelectronics,2016,78:344-350.
[43]DONG B,SONG X Z,KONG X Q,et al.Simultaneous Near-Infrared and Two-Photon in Vivo Imaging of H2O2 Using a Ratiometric Fluorescent Probe Based on the Unique Oxidative Rearrangement of Oxonium[J].Advanced Materials,2016,28(39):8755-8759.
[44]CHENG D,PAN Y,WANG L,et al.Selective Visualization of the Endogenous Peroxynitrite in an Inflamed Mouse Model by a Mitochondria-Targetable Two-Photon Ratiometric Fluorescent Probe[J].Journal of the American Chemical Society,2017,139(1):285-292.
[45]ZHOU L,ZHANG X,WANG Q,et al.Molecular Engineering of a TBET-Based Two-Photon Fluorescent Probe for Ratiometric Imaging of Living Cells and Tissues[J].Journal of the American Chemical Society,2014,136(28):9838-9841.
[46]ZHOU L,WANG Q,ZHANG X B,et al.ThroughBond Energy Transfer-Based Ratiometric Two-Photon Probe for Fluorescent Imaging of Pd2+Ions in Living Cells and Tissues[J].Analytical Chemistry,2015,87(8):4503-4507.
[47]ZHOU L Y,LIU Y C,HU S Q,et al.A New Ratiometric Two-Photon Fluorescent Probe for Imaging of Lysosomes in Living Cells and Tissues[J].Tetrahedron,2016,72(31):4637-4642.
[48]WANG J,LI B,ZHAO W,et al.Two-Photon Near Infrared Fluorescent Turn-On Probe Toward Cysteine and Its Imaging Applications[J].ACS Sensors,2016,1(7):882-887.
[49]SUN W,FAN J L,HU C,et al.A Two-Photon Fluorescent Probe with Near-Infrared Emission for Hydrogen Sulfide Imaging in Biosystems[J].Chemical Communications,2013,49(37):3890-3892.
[50]ZHOU L Y,LU D Q,WANG Q Q,et al.Molecular Engineering of a Mitochondrial-Targeting Two-Photon in and Near-Infrared Out Fluorescent Probe for Gaseous Signal Molecules H2S in Deep Tissue Bioimaging[J].Biosensors and Bioelectronics,2017,91:699-705.
[51]ZHOU L Y,WANG Q Q,TAN Y,et al.Rational Development of Near-Infrared Fluorophores with Large Stokes Shifts,Bright One-Photon and Two-Photon Emissions for Bioimaging and Biosensing Applications[J].Chemistry-A European Journal,2017,23(36):8736-8740.